If your finances are in order; if your business is booming, so much so that it detracts from your day job; if you have a spouse with health insurance (huge plus!); if you’re comfortable with uncertainty; and if you are prepared to meticulously document hours, receipts and other expenses. Then and only then are you really ready to rock this thing the right way.

Or, in my case, if your employer is shutting down your site and moving operations to another state. But ideally you’d have the nitty-gritty details nailed down regardless.

This is a tough one. I was laid-off, so I didn’t exactly choose, though I had a 3-month lead-time of notice, and I knew I was getting a severance as a cushion. Pairing that with having steady work from a main client, I felt I was ready. I think the most sensible thing is to come up with a level of income you’re comfortable with getting from outside clients, and a level of savings that can get you through 3-6 months of expenses, get your starter plan in order and plan your out-the-gate marketing onslaught… and then do it!

Are you on the fence? Wondering if you’re ready or waiting for some sign to tell you it’s time? Some have used the Creative Freelancer Conference as their “launch date” and you can too: it’s June 23-24 in Chicago and we’ll be recognizing everyone who is (or has) launched their business at the conference. You can be one of them too! (Early-bird registration ends April 1. Set that as you deciding date.)